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. Author manuscript; available in PMC: 2018 Feb 2.
Published in final edited form as: Mol Pharm. 2017 Aug 31;14(10):3248–3257. doi: 10.1021/acs.molpharmaceut.7b00231

Scheme 3. Synthesis of Compounds 2 and 5a.

Scheme 3

aReagents and conditions: (i) Eschenmoser’s salt, BnOH, 70 °C, 21 h. (ii) Diethyl phosphite, Al(CH3)3, DCM, 0 °C to rt, 16 h. (iii) Phenylsilane, Pd(PPh3)4, THF, rt, 1 h. (iv) For 17a: POC-Cl, Nal, K2CO3, acetonitrile, rt to 50 °C, overnight. For 17b: C8H17Br, Nal, K2CO3, acetonitrile, rt to 50 °C, overnight. (v) (1) TMS-Br, DCM, 0 °C to rt, 18 h; (2) Pb/C, H2 (balloon), THF, rt, 22 h.